CA2216617C - Nouveaux derives de flavones, leur procede de preparation et les compositions pharmaceutiques qui les contiennent - Google Patents
Nouveaux derives de flavones, leur procede de preparation et les compositions pharmaceutiques qui les contiennent Download PDFInfo
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- CA2216617C CA2216617C CA002216617A CA2216617A CA2216617C CA 2216617 C CA2216617 C CA 2216617C CA 002216617 A CA002216617 A CA 002216617A CA 2216617 A CA2216617 A CA 2216617A CA 2216617 C CA2216617 C CA 2216617C
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- radical
- alkyl
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- 238000000034 method Methods 0.000 title claims description 17
- 238000002360 preparation method Methods 0.000 title claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 7
- 150000002212 flavone derivatives Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 82
- 125000005843 halogen group Chemical group 0.000 claims abstract description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 12
- 125000004429 atom Chemical group 0.000 claims abstract description 12
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 12
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 11
- 239000001301 oxygen Substances 0.000 claims abstract description 11
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 6
- 125000004434 sulfur atom Chemical group 0.000 claims abstract 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract 2
- -1 alkyl radical Chemical class 0.000 claims description 144
- 229960001876 diosmetin Drugs 0.000 claims description 36
- MBNGWHIJMBWFHU-UHFFFAOYSA-N diosmetin Chemical compound C1=C(O)C(OC)=CC=C1C1=CC(=O)C2=C(O)C=C(O)C=C2O1 MBNGWHIJMBWFHU-UHFFFAOYSA-N 0.000 claims description 30
- 150000003254 radicals Chemical class 0.000 claims description 29
- 239000002253 acid Substances 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 150000005840 aryl radicals Chemical class 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 230000003287 optical effect Effects 0.000 claims description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 239000012298 atmosphere Substances 0.000 claims description 4
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Chemical compound CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 claims description 3
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000002571 phosphodiesterase inhibitor Substances 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 229940099471 Phosphodiesterase inhibitor Drugs 0.000 claims 1
- BQOWUDKEXDCGQS-UHFFFAOYSA-N [CH]1CCCC1 Chemical compound [CH]1CCCC1 BQOWUDKEXDCGQS-UHFFFAOYSA-N 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 abstract description 14
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 abstract description 14
- 239000003112 inhibitor Substances 0.000 abstract description 3
- 238000002560 therapeutic procedure Methods 0.000 abstract 1
- 238000002844 melting Methods 0.000 description 36
- 230000008018 melting Effects 0.000 description 36
- QAGGICSUEVNSGH-UHFFFAOYSA-N Diosmetin Natural products C1=C(O)C(OC)=CC=C1C1=CC(=O)C2=CC=C(O)C=C2O1 QAGGICSUEVNSGH-UHFFFAOYSA-N 0.000 description 29
- 235000015428 diosmetin Nutrition 0.000 description 29
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 238000011282 treatment Methods 0.000 description 8
- 238000007792 addition Methods 0.000 description 7
- 230000005764 inhibitory process Effects 0.000 description 7
- 239000012429 reaction media Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 230000001225 therapeutic effect Effects 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 5
- 235000015497 potassium bicarbonate Nutrition 0.000 description 5
- 239000011736 potassium bicarbonate Substances 0.000 description 5
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 5
- SULYEHHGGXARJS-UHFFFAOYSA-N 2',4'-dihydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1O SULYEHHGGXARJS-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- ZOOGRGPOEVQQDX-UHFFFAOYSA-N cyclic GMP Natural products O1C2COP(O)(=O)OC2C(O)C1N1C=NC2=C1NC(N)=NC2=O ZOOGRGPOEVQQDX-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 description 3
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- IVOMOUWHDPKRLL-UHFFFAOYSA-N UNPD107823 Natural products O1C2COP(O)(=O)OC2C(O)C1N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229930003935 flavonoid Natural products 0.000 description 3
- 150000002215 flavonoids Chemical class 0.000 description 3
- 235000017173 flavonoids Nutrition 0.000 description 3
- 125000006203 morpholinoethyl group Chemical group [H]C([H])(*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 2
- PAQZWJGSJMLPMG-UHFFFAOYSA-N 2,4,6-tripropyl-1,3,5,2$l^{5},4$l^{5},6$l^{5}-trioxatriphosphinane 2,4,6-trioxide Chemical compound CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1 PAQZWJGSJMLPMG-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
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- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
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- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
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- 229950005741 rolipram Drugs 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9611808A FR2753969B1 (fr) | 1996-09-27 | 1996-09-27 | Nouveaux derives de flavones, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR96.11808 | 1996-09-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2216617A1 CA2216617A1 (fr) | 1998-03-27 |
| CA2216617C true CA2216617C (fr) | 2002-12-03 |
Family
ID=9496129
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002216617A Expired - Fee Related CA2216617C (fr) | 1996-09-27 | 1997-09-26 | Nouveaux derives de flavones, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US5889003A (pt) |
| EP (1) | EP0832886B1 (pt) |
| JP (1) | JPH10114766A (pt) |
| CN (1) | CN1094936C (pt) |
| AT (1) | ATE227712T1 (pt) |
| AU (1) | AU728990B2 (pt) |
| BR (1) | BR9704900A (pt) |
| CA (1) | CA2216617C (pt) |
| DE (1) | DE69717044T2 (pt) |
| DK (1) | DK0832886T3 (pt) |
| ES (1) | ES2187738T3 (pt) |
| FR (1) | FR2753969B1 (pt) |
| HU (1) | HUP9701588A3 (pt) |
| NO (1) | NO974455L (pt) |
| NZ (1) | NZ328858A (pt) |
| PL (1) | PL322297A1 (pt) |
| PT (1) | PT832886E (pt) |
| ZA (1) | ZA978652B (pt) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE298566T1 (de) * | 1995-09-11 | 2005-07-15 | Osteoarthritis Sciences Inc | Proteintyrosine-kinaseinhibitoren zur behandlung der osteoarthritis |
| MY126544A (en) | 1998-08-26 | 2006-10-31 | Smithkline Beecham Corp | Therapies for treating pulmonary diseases |
| CA2345311A1 (en) * | 1998-09-24 | 2000-03-30 | Kazutoshi Watanabe | Hydroxyflavone derivatives as tau protein kinase 1 inhibitors |
| DE60043318D1 (de) | 1999-08-21 | 2010-01-14 | Nycomed Gmbh | Synergistische kombination von pumafentrine und salmeterol |
| US6806257B1 (en) | 1999-10-20 | 2004-10-19 | Board Of Trustees Of Southern Illinois University | Flavones as inducible nitric oxide synthase inhibitors, cyclooxygenase-2 inhibitors and potassium channel activators |
| US6334998B1 (en) | 1999-12-07 | 2002-01-01 | Parker Hughes Institute | Estrogens for treating ALS |
| EP1127572A3 (en) * | 2000-02-25 | 2003-05-02 | Basf Aktiengesellschaft | Use of flavones for treating cycloxygenase-2 mediated diseases |
| US6472436B1 (en) * | 2000-07-17 | 2002-10-29 | The Salk Institute For Biological Studies | Methods for protecting cells from amyloid toxicity and for inhibiting amyloid protein production |
| DE10104350A1 (de) * | 2001-02-01 | 2002-08-14 | Merck Patent Gmbh | Verfahren zur Herstellung von Flavon Derivaten |
| DE10232595A1 (de) * | 2002-07-18 | 2004-02-05 | Merck Patent Gmbh | Lichtschutzmittel |
| KR20050115331A (ko) | 2003-04-01 | 2005-12-07 | 어플라이드 리서치 시스템스 에이알에스 홀딩 엔.브이. | 불임증 포스포디에스터라제의 억제제 |
| JP5058481B2 (ja) * | 2005-11-28 | 2012-10-24 | 丸善製薬株式会社 | 角化細胞増殖剤、サイクリックａｍｐホスホジエステラーゼ阻害剤、及び保湿剤 |
| EP2058310A4 (en) * | 2006-09-01 | 2010-11-17 | Kyorin Seiyaku Kk | PYRAZOLOPYRIDINCARBOXYL ACID AMID DERIVATIVE AND THE DERIVATIVELY PHOSPHODIESTERASE (PDE) INHIBITOR |
| CN101148444A (zh) * | 2006-09-20 | 2008-03-26 | 上海特化医药科技有限公司 | 黄酮衍生物、制备方法及应用 |
| KR100930467B1 (ko) * | 2007-06-07 | 2009-12-08 | 동아제약주식회사 | 점액분비를 촉진시키는 3',4',5-트리메톡시 플라본 유도체화합물, 그의 제조방법 및 약학적 용도 |
| JP4559531B1 (ja) * | 2009-12-03 | 2010-10-06 | ウシオケミックス株式会社 | ノビレチンの製造方法 |
| CN103059005B (zh) * | 2012-11-22 | 2015-04-22 | 中南民族大学 | 白杨素酰胺衍生物及其医药用途 |
| CN105906598B (zh) * | 2016-05-19 | 2018-05-08 | 江苏耐雀生物工程技术有限公司 | 白杨素衍生物及其制备方法和应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2623808B1 (fr) * | 1987-12-01 | 1990-03-09 | Adir | Nouveaux derives flavonoides (benzyl-4 piperazinyl-1)-2 oxo-2 ethylene substitues, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2689127B1 (fr) * | 1992-03-31 | 1994-05-06 | Adir Cie | Nouvelles 3', 5' -ditertbutyl-4'-hydroxy flavones, leur procede de preparation et les compositions pharmaceutiques les renfermant. |
| FR2748025B1 (fr) * | 1996-04-25 | 1998-10-30 | Adir | Nouveaux acides et esters de la diosmetine, et les compositions pharmaceutiques les contenant |
-
1996
- 1996-09-27 FR FR9611808A patent/FR2753969B1/fr not_active Expired - Fee Related
-
1997
- 1997-09-23 DK DK97402202T patent/DK0832886T3/da active
- 1997-09-23 AT AT97402202T patent/ATE227712T1/de not_active IP Right Cessation
- 1997-09-23 DE DE69717044T patent/DE69717044T2/de not_active Expired - Fee Related
- 1997-09-23 ES ES97402202T patent/ES2187738T3/es not_active Expired - Lifetime
- 1997-09-23 EP EP97402202A patent/EP0832886B1/fr not_active Expired - Lifetime
- 1997-09-23 PT PT97402202T patent/PT832886E/pt unknown
- 1997-09-25 PL PL97322297A patent/PL322297A1/xx unknown
- 1997-09-26 NO NO974455A patent/NO974455L/no not_active Application Discontinuation
- 1997-09-26 JP JP9261323A patent/JPH10114766A/ja active Pending
- 1997-09-26 NZ NZ328858A patent/NZ328858A/en unknown
- 1997-09-26 CN CN97120535A patent/CN1094936C/zh not_active Expired - Fee Related
- 1997-09-26 AU AU39271/97A patent/AU728990B2/en not_active Ceased
- 1997-09-26 HU HU9701588A patent/HUP9701588A3/hu unknown
- 1997-09-26 ZA ZA9708652A patent/ZA978652B/xx unknown
- 1997-09-26 BR BR9704900A patent/BR9704900A/pt not_active IP Right Cessation
- 1997-09-26 CA CA002216617A patent/CA2216617C/fr not_active Expired - Fee Related
- 1997-09-26 US US08/968,837 patent/US5889003A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| AU728990B2 (en) | 2001-01-25 |
| ES2187738T3 (es) | 2003-06-16 |
| FR2753969B1 (fr) | 1998-10-30 |
| HUP9701588A3 (en) | 1999-03-01 |
| NZ328858A (en) | 1998-01-26 |
| EP0832886B1 (fr) | 2002-11-13 |
| PL322297A1 (en) | 1998-03-30 |
| JPH10114766A (ja) | 1998-05-06 |
| CA2216617A1 (fr) | 1998-03-27 |
| NO974455L (no) | 1998-03-30 |
| FR2753969A1 (fr) | 1998-04-03 |
| US5889003A (en) | 1999-03-30 |
| HU9701588D0 (en) | 1997-11-28 |
| ATE227712T1 (de) | 2002-11-15 |
| CN1094936C (zh) | 2002-11-27 |
| DE69717044D1 (de) | 2002-12-19 |
| AU3927197A (en) | 1998-04-02 |
| HUP9701588A2 (hu) | 1998-12-28 |
| ZA978652B (en) | 1998-03-27 |
| BR9704900A (pt) | 1998-10-27 |
| CN1179422A (zh) | 1998-04-22 |
| PT832886E (pt) | 2003-03-31 |
| DE69717044T2 (de) | 2003-07-24 |
| NO974455D0 (no) | 1997-09-26 |
| DK0832886T3 (da) | 2003-03-10 |
| EP0832886A1 (fr) | 1998-04-01 |
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| EEER | Examination request | ||
| MKLA | Lapsed |